628-71-7

Basic information

• Product Name: 1-Heptyne
• Synonyms: Amylacetylene;hept-1-yne;n-C5H11CequivCH;N-AMYLACETYLENE;1-HEPTYNE;HEPTYNE(1-);1-Heptyne99%;1-Heptyne 99%
• CAS NO: 628-71-7
• Molecular Formula: C₇H₁₂
• Molecular Weight: 96.17
• EINECS: 211-051-5
• Product Categories: Alkynes;Organic Building Blocks;Terminal;Miscellaneous;Acetylenes;Acetylenic Hydrocarbons
• Mol File: 628-71-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: -81 °C
• Boiling Point: 99-100 °C(lit.)
• Flash Point: 28 °F
• Appearance: Clear colorless to light yellow-green/Liquid
• Density: 0.733 g/mL at 25 °C(lit.)
• Vapor Pressure: 93.1 mm Hg ( 37.7 °C)
• Refractive Index: n20/D 1.408(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Soluble in organic solvents. Insoluble in water.
• BRN: 1733518
• CAS DataBase Reference: 1-Heptyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Heptyne(628-71-7)
• EPA Substance Registry System: 1-Heptyne(628-71-7)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-36/37/38-65
• Safety Statements: 16-26-36-62-9-33
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 628-71-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow-green liquid

Uses

1-Heptyne is used in the synthesis of (6Z,10E,12Z)-octadeca-6,10,12-trienoic acid and (8Z,12E,14Z)-eicosa-8,12,14-trienoic acid.

General Description

The hydrogenation of 1-heptyne with palladium, platinum and ruthenium supported on activated carbon as catalysts, was studied.

InChI:InChI=1/C7H12/c1-3-5-7-6-4-2/h1H,4-7H2,2H3

Synthetic route

oct-2-ynoic acid (5663-96-7) → 1-Heptyne (628-71-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0)	100%

1,2-dibromoheptane (42474-21-5) → 1-Heptyne (628-71-7)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 60℃; for 2h;	98%
With tetrabutyl-ammonium chloride; potassium hydroxide In water at 140℃; for 4h;	86.4%
With potassium hydroxide; 2,5-dimethyl-2,5-hexanediol; tetraoctyl ammonium bromide at 80 - 90℃; for 0.25h;	85%
With potassium hydroxide; mineral oil at 250℃;
With tetralin; anion-exchanger at 160℃;

1,2-Heptadiene (2384-90-9) → 1-Heptyne (628-71-7) + hept-2-yne (1119-65-9)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate at 70℃; for 2h;	A 2% B 93%

1,2-dichloro-heptane (10575-87-8) → 1-Heptyne (628-71-7)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In Petroleum ether at 80℃; for 8h;	86%
With potassium hydroxide; mineral oil at 250℃;

1-Bromopentane (110-53-2) + acetylene (74-86-2) → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia; sodium at -40 - 20℃;	80%

1-(benzotriazol-1-yl)-2-heptanone p-tosylhydrazone (189343-56-4) → 1-Heptyne (628-71-7)

Conditions	Yield
With n-butyllithium In diethyl ether 1) -78 deg C, 0.5 h; 2) rt, 48 h;	73%

heptanal (111-71-7) → 1-Heptyne (628-71-7)

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane In N,N-dimethyl-formamide at -10 - 20℃;	66%
With phosphorus pentachloride
Multi-step reaction with 2 steps 1: PCl5 2: alcoholic potash / 150 °C View Scheme

1-heptynyl chloride (51556-10-6) + butyl magnesium bromide (693-04-9) → 1-Heptyne (628-71-7) + tetradeca-6,8-diyne (16387-72-7)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; copper dichloride In tetrahydrofuran at 0℃; for 1.25h; Inert atmosphere;	A 55% B 35%

chloroacetic acid (79-11-8) + (Z)-1-methylthio-2-triphenylstannylhept-1-ene (351500-79-3) → methylthiol (74-93-1) + diphenyltin di(monochloroacetate) (30250-06-7) + 1-Heptyne (628-71-7) + benzene (71-43-2)

Conditions	Yield
In not given	A 0% B 30% C 5% D n/a

1-Chloropentane (543-59-9) + 1-Bromopentane (110-53-2) + sodium acetylide (1066-26-8) → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia

1-Chloropentane (543-59-9) + sodium acetylide (1066-26-8) → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia

1,1-dichloroheptane (821-25-0) → 1-Heptyne (628-71-7)

Conditions	Yield
With potassium carbonate at 150℃;
With potassium hydroxide; mineral oil at 250℃;
With soda lime at 420℃; Zersetzen der erhaltenen Produkte mit Wasser;

4-chloro-hept-3-ene (2431-24-5) → hept-3-yne (2586-89-2) + 1-Heptyne (628-71-7)

Conditions	Yield
With sodium amide; xylene at 130℃;
With 1,2,4-Trimethylbenzene; sodium amide at 140℃;

sulfuric acid dibutyl ester (625-22-9) + propargyl magnesium bromide (18295-60-8) → 1-Heptyne (628-71-7) + 1,2-Heptadiene (2384-90-9)

(E)/(Z)-1-bromo-1-heptene (89942-12-1) + sodium ethanolate (141-52-6) → 1-Heptyne (628-71-7)

Conditions	Yield
mixture of cis-and trans-1-bromo-heptene-(1);

(E)/(Z)-1-bromo-1-heptene (89942-12-1) → 1-Heptene (592-76-7) + 1-Heptyne (628-71-7)

Conditions	Yield
With sodium; xylene at 25℃;

(E)/(Z)-1-bromo-1-heptene (89942-12-1) → 1-Heptyne (628-71-7)

Conditions	Yield
With potassium hydroxide; mineral oil at 250℃;

1-Bromopentane (110-53-2) + sodium acetylide (1066-26-8) → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia
With tetrahydrofuran; N,N-dimethyl-formamide
In ammonia at -60℃;
With ammonia

amyl iodide (628-17-1) + sodium acetylide (1066-26-8) → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia at 20℃; man verwandelt das Reaktionsprodukt mit Natriumammonium in die Natriumverbindung und zersetzt diese durch Wasser;

hept-3-yne (2586-89-2) → 1-Heptyne (628-71-7)

Conditions	Yield
With 1,2,4-Trimethylbenzene; sodium amide at 170℃;

1,2-Heptadiene (2384-90-9) → 1-Heptyne (628-71-7)

Conditions	Yield
With sodium amide; paraffin oil at 140℃;

1-chloro-hept-1-ene (2384-75-0) → 1-Heptyne (628-71-7)

Conditions	Yield
With potassium hydroxide; mineral oil at 250℃;
With sodium amide; paraffin oil at 150 - 155℃; und zersetzt man das Reaktionsprodukt mit Wasser;
With sodium amide; toluene at 100 - 130℃; und zersetzt man das Reaktionsprodukt mit Wasser;
With sodium amide; xylene at 100 - 130℃; und zersetzt man das Reaktionsprodukt mit Wasser;

3-bromo-hept-1-yne (61996-78-9) → 1-Heptyne (628-71-7) + 1,2-Heptadiene (2384-90-9)

Conditions	Yield
With ethanol; coppered zinc
With lithium aluminium tetrahydride; diethyl ether
With amalgamated magnesium; diethyl ether anschliessend mit wss.Ammoniumchlorid;

1,1,-dichloro-1-heptene (32363-95-4) → 1-Heptyne (628-71-7)

Conditions	Yield
With diethyl ether; sodium

1,1-dibromohept-1-ene (32363-96-5) + sodium ethanolate (141-52-6) → 1-Heptyne (628-71-7)

1,1-dibromohept-1-ene (32363-96-5) → 1-Heptyne (628-71-7)

Conditions	Yield
With potassium hydroxide; mineral oil at 250℃;
With sodium ethanolate

(Z)-1,2-dibromohept-1-ene → 1-Heptyne (628-71-7)

Conditions	Yield
With ammonia; sodium amide anschliessendes Zersetzen mit Ammoniumnitrat;

n-butyl magnesium bromide (693-03-8) + diethyl ether (60-29-7) + propargyl bromide (106-96-7) → 1-Heptyne (628-71-7) + 1,2-Heptadiene (2384-90-9)

Conditions	Yield
at -15℃; analoge Reaktionen mit Alkyl-, Alkenyl-, Alkinyl- und Arylmagnesiumbromiden und Einfluss von Temp. und Loesungsm. (Ae. oder Tetrahydrofuran);

(E)/(Z)-1-bromo-1-heptene (89942-12-1) + aniline (62-53-3) → 1-Heptyne (628-71-7)

Conditions	Yield
mixture of cis-and trans-1-bromo-heptene-(1);

p-nitrobenzene iodide (636-98-6) + 1-Heptyne (628-71-7) → 1-(hept-1-ynyl)-4-nitrobenzene (64146-60-7)

Conditions	Yield
With copper(l) iodide; iodophenylbis(triphenylphosphine)palladium; triethylamine In chloroform at 60℃; for 1h;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tributyl-amine; potassium carbonate In water at 20℃; for 4h;	95%
With piperidine; 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene; tetrabutylammomium bromide; palladium diacetate In water; N,N-dimethyl-formamide at 40℃; for 3h; Sonogashira Cross-Coupling;	94%

1-Heptyne (628-71-7) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(1-hept-1-ynyl)benzonitrile (64146-59-4)

Conditions	Yield
With copper(I) bromide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 90℃; for 0.166667h;	100%
With nickel(II) ferrite; potassium carbonate In water at 100℃; for 2.25h; Sonogashira Cross-Coupling;	87%
With copper(I) bromide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20℃; Rate constant;

1-Heptyne (628-71-7) → tetradeca-6,8-diyne (16387-72-7)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; air; palladium diacetate; copper(l) iodide In acetonitrile at 20℃; for 2h;	100%
With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 25℃; for 24h;	96%
With copper(I) oxide In dimethyl sulfoxide at 110℃; for 2h;	96%

1-Heptyne (628-71-7) + carbon monoxide (201230-82-2) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → (3aR,4S,7R,7aR)-2-Pentyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one (85806-43-5, 85806-49-1, 122422-23-5, 122422-24-6)

Conditions	Yield
dodecacarbonyl tetracobalt In dichloromethane at 150℃; under 7600 Torr; for 6h;	100%
Co/C In tetrahydrofuran at 130℃; under 22800 Torr; for 18h; Pauson-Khand reaction;	98%
Pauson-Khand reaction;	64%

1-Heptyne (628-71-7) → trans-1-heptenylboronic acid (57404-76-9)

Conditions	Yield
With benzo[1,3,2]dioxaborole In tetrahydrofuran Heating;	100%
Stage #1: 1-Heptyne With dibromoborane dimethylsulfide In dichloromethane at 0℃; Stage #2: With sodium hydroxide In dichloromethane Stage #3: With ammonium chloride In dichloromethane Further stages.;	78%
Stage #1: 1-Heptyne With dibromoborane-methyl sulfide complex In dichloromethane at 20℃; for 4h; Stage #2: With water In diethyl ether; dichloromethane at 20℃; for 0.25h;	74%

2-bromo-6-methylpyridine (5315-25-3) + 1-Heptyne (628-71-7) → 2-(hept-1-yn-1-yl)-6-methylpyridine (334026-55-0)

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 60℃; for 1.5h;	100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃; Inert atmosphere;	100%

1-Heptyne (628-71-7) + bis(pinacol)diborane (73183-34-3) → (E)-2,2′-(hept-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
With tris(bicyclo[2.2.1]heptene)palladium; triphenylphosphine at 20℃; for 12h;	100%
With gold nanoparticles supported on titanium dioxide at 65℃; for 2h; chemoselective reaction;	91%
With methanol; potassium carbonate In diethyl ether at 40℃; for 12h; Inert atmosphere; chemoselective reaction;	72%

1-Heptyne (628-71-7) + tert-butyl-(1-decyl-4-iodo-but-3-enyloxy)-dimethyl-silane (502150-94-9) → tert-butyl-(1-decyl-undec-3-en-5-ynyloxy)-dimethyl-silane (502150-95-0)

Conditions	Yield
With piperidine; copper(l) iodide; dichloro bis(acetonitrile) palladium(II) at 20℃; Sonogashira coupling;	100%

1-Heptyne (628-71-7) + 4-methoxy-benzaldehyde (123-11-5) → 1-(4-methoxyphenyl)oct-1-yn-1-ol (371256-71-2)

Conditions	Yield
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere;	100%
Stage #1: 1-Heptyne With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane at -30℃; for 2h; Stage #2: 4-methoxy-benzaldehyde In tetrahydrofuran; hexane at -10℃; Further stages.;	96%
With ethylmagnesium bromide

1-Heptyne (628-71-7) + 4-methoxy-2-(trifluoro-methanesulfonyloxy)-benzoic acid methyl ester (216768-18-2) → methyl 2-(1-heptyn-1-yl)-4-(methyloxy)benzoate (872549-78-5)

Conditions	Yield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride Sonogashira Coupling;	100%

{4-(4-iodobenzoyloxy)butyl}trimethylammonium bistrifluoromethanesulfonimidate (827027-40-7) + 1-Heptyne (628-71-7) → C2F6NO4S2(1-)*C21H32NO2(1+) (827027-80-5)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 1h; Product distribution / selectivity; Sonogashira Coupling;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In dichloromethane at 40℃; for 1h; Product distribution / selectivity; Sonogashira Coupling;	100%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In 1,4-dioxane at 40℃; for 1h; Product distribution / selectivity; Sonogashira Coupling;	100%

1-Heptyne (628-71-7) + (1R,2R,3S,4R)-4-azido-1-<((tert-butyldiphenylsilyl)oxy)methyl>-2,3-(isopropylidenedioxy)cyclopentane (112543-78-9) → (1R,2S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-isopropylidenedioxy-1-[4-pentyl-1H-1,2,3-triazol-1-yl]cyclopentane (1161113-44-5)

Conditions	Yield
With copper; copper(II) sulfate In water; tert-butyl alcohol at 125℃; for 0.25h; Microwave irradiation;	100%

1-Heptyne (628-71-7) + trifluoro-methanesulfonic acid 3-methoxy-2-methyl-6-nitro-phenyl ester (835883-30-2) → C15H19NO3 (1148008-97-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetra-(n-butyl)ammonium iodide In triethylamine; acetonitrile Sonogashira-Hagihara coupling; Reflux;	100%

1-Heptyne (628-71-7) + 2-Methoxybenzoyl chloride (21615-34-9) → (E)-3-chloro-1-(2-hydroxyphenyl)oct-2-en-1-one

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 23℃; for 4h; Inert atmosphere;	100%

formaldehyd (50-00-0) + 1-Heptyne (628-71-7) → 2-octyn-1-ol (20739-58-6)

Conditions	Yield
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: formaldehyd In tetrahydrofuran at -78 - 20℃; for 26h;	99%
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 5h;	94%
Stage #1: 1-Heptyne With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -30℃; for 1h; Stage #2: formaldehyd In tetrahydrofuran; hexane at -30℃; for 2h; Further stages.;	90%

2-bromo-pyridine (109-04-6) + 1-Heptyne (628-71-7) → 2-(hept-1-yn-1-yl)pyridine (49836-16-0)

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 75℃; for 12h; Inert atmosphere;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Sonogashira Cross-Coupling; Inert atmosphere;	92%
With copper(I) bromide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 90℃; for 0.333333h;	81%
With palladium 10% on activated carbon; potassium carbonate; triphenylphosphine In ethanol for 48h; Reflux; Green chemistry;	77%

1-Heptyne (628-71-7) + cyclohexanone (108-94-1) → 1-(1-heptynyl)cyclopentan-1-ol (37828-64-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane 0 deg C, 75 min then rt., 3.5 h;	99%
With sodium aluminum diethyl dihydride 1.) toluene, r.t., 3 h, 2.) toluene, 0 deg C, 1 h; Yield given. Multistep reaction;
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran Stage #2: cyclohexanone In water

1-Heptyne (628-71-7) + benzoyl chloride (98-88-4) → 1-phenyloct-2-yn-1-one (27259-10-5)

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) for 15h; Ambient temperature;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere;	99%
With copper(l) iodide; di-μ-chlorobis{hydrogen bis(diphenylphosphito)(1-)-P,P'}dipalladium; triethylamine In toluene at 80℃; for 18h; Inert atmosphere;	93%

1-Heptyne (628-71-7) + 9-(3-iodo-benzyl)-9H-purin-6-ylamine (220582-68-3) → 9-<3-(1-heptynyl)benzyl>-9H-6-purinamine (220582-73-0)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In various solvent(s) for 0.75h; Heating;	99%

1-Heptyne (628-71-7) + 2-iodophenylamine (615-43-0) → 2-(hept-1-ynyl)benzeneamine (118476-12-3)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 2h; Sonogashira coupling reaction;	99%
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In diethylamine at 30℃; for 24h;	98%
Stage #1: 2-iodophenylamine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 30℃; for 0.166667h; Inert atmosphere; Stage #2: 1-Heptyne at 30℃; for 24h; Inert atmosphere;	98%

1-Heptyne (628-71-7) + 4-acetoxyiodobenzene (33527-94-5) → acetic acid 4-hept-1-ynyl-phenyl ester

Conditions	Yield
With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 3h;	99%

piperidine (110-89-4) + 1-Heptyne (628-71-7) + benzaldehyde (100-52-7) → 1-(1-phenyloct-2-yn-1-yl)piperidine

Conditions	Yield
With [copper(I)]2[(2-picolyliminomethyl)pyrrole]2 In toluene at 110℃; for 2h; Inert atmosphere;	99%
With zinc diacetate In toluene for 7h; Heating;	89%
With [bmim]PF6 at 120℃; for 2h;	83 % Chromat.
With nano Co3O4 In toluene at 130℃; for 15h; Sealed tube;	10 %Chromat.

1-Heptyne (628-71-7) + 4-iodo-2-nitrotoluene (41252-97-5) → 1-(4-methyl-3-nitrophenyl)hept-1-yne

Conditions	Yield
With copper(l) iodide; diisopropylamine; triphenylphosphine; palladium on activated charcoal In N,N-dimethyl-formamide at 100℃; for 16h; Sonogashira reaction;	99%

1-Heptyne (628-71-7) + benzyl azide (622-79-7) → 4-pentyl-1-(phenylmethyl)-1H-1,2,3-triazole (1033749-58-4)

Conditions	Yield
With Cu98Mn2 nanoporous catalyst In toluene at 65℃; for 6h; Huisgen cycloaddition; regioselective reaction;	99%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 24h;	99%
With copper-supported ionic liquid catalyst In ethanol; water at 20℃; for 1.5h; Huisgen cycloaddition;	98%

1-Heptyne (628-71-7) + ortho-bromobenzaldehyde (6630-33-7) → 2-(hept-1-yn-1-yl)benzaldehyde

Conditions	Yield
With copper(l) iodide; bis(triphenylylphosphine)palladium(II) dichloride; triethylamine at 50℃; for 5h;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 4h; Sonogashira coupling; Inert atmosphere;	91%
Stage #1: 1-Heptyne; ortho-bromobenzaldehyde With bis-triphenylphosphine-palladium(II) chloride; triethylamine at 20℃; for 0.25h; Sonogashira coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 4h; Sonogashira coupling; Inert atmosphere;	91%

1-Heptyne (628-71-7) + benzyl bromide (100-39-0) → 4-pentyl-1-(phenylmethyl)-1H-1,2,3-triazole (1033749-58-4)

Conditions	Yield
With sodium azide In water at 20℃; for 1.5h; Huisgen Cycloaddition; Green chemistry;	99%
With sodium azide; sodium L-ascorbate In water; tert-butyl alcohol for 4h; Heating; Green chemistry;	96%
With sodium azide; sodium L-ascorbate In water; tert-butyl alcohol at 55℃; for 4h; Huisgen Cycloaddition; Green chemistry; regioselective reaction;	95%

paraformaldehyde-d2 (1664-98-8) + 1-Heptyne (628-71-7) → 1,1-[2H2]-oct-2-yn-1-ol (144401-62-7)

Conditions	Yield
Stage #1: 1-Heptyne With ethyl bromide; magnesium In tetrahydrofuran Inert atmosphere; Stage #2: paraformaldehyde-d2 In tetrahydrofuran for 2h; Reflux; Stage #3: With sulfuric acid In tetrahydrofuran; water Cooling with ice;	99%
Stage #1: 1-Heptyne With ethylmagnesium bromide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: paraformaldehyde-d2 In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	40%
Stage #1: 1-Heptyne With ethylmagnesium bromide In tetrahydrofuran Inert atmosphere; Stage #2: paraformaldehyde-d2 In tetrahydrofuran for 2h; Inert atmosphere; Reflux;
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: paraformaldehyde-d2 In tetrahydrofuran; water at -20 - 20℃; for 18h;

1-Heptyne (628-71-7) + 4β-azido-4-deoxy-4′-demethylepipodophyllotoxin (117604-05-4) → 4'-O-demethyl-4β-[(4-pentyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin (1310548-40-3)

Conditions	Yield
With copper(ll) sulfate pentahydrate; L-ascorbic acid sodium salt In water; tert-butyl alcohol at 20℃; for 8h;	99%

2-amino-5-iodopyrimidine (1445-39-2) + 1-Heptyne (628-71-7) → 5-(hept-1-ynyl)pyrimidin-2-amine (1361537-65-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Sonogashira coupling; Inert atmosphere; Reflux;	99%

Upstream product

• 111-71-7 heptanal 
• 543-59-9 1-Chloropentane 
• 110-53-2 1-Bromopentane 
• 1066-26-8 sodium acetylide 
• 10575-87-8 1,2-dichloro-heptane 
• 821-25-0 1,1-dichloroheptane 
• 2431-24-5 4-chloro-hept-3-ene 
• 625-22-9 sulfuric acid dibutyl ester 
• 18295-60-8 propargyl magnesium bromide 
• 592-76-7 1-Heptene 
• 2384-90-9 1,2-Heptadiene 
• 32363-95-4 1,1,-dichloro-1-heptene 
• 80359-12-2 sodium triethylheptynylgallate 
• 1846-68-0 oct-2-ynal 

Downstream Products

• 106-73-0 methyl heptanoate 
• 71899-44-0 octadec-6-yne 
• 7333-25-7 10,12-octadecadiynoic acid 
• 110-43-0 n-pentyl methyl ketone 
• 16387-55-6 1,1-diethoxy-2-octyne 
• 20739-58-6 2-octyn-1-ol 
• 26547-25-1 non-3-yn-2-ol 
• 592-76-7 1-Heptene 
• 142-82-5 n-heptane 
• 187737-37-7 propene 
• 34557-54-5 methane 
• 74-85-1 ethene 
• 2384-90-9 1,2-Heptadiene 
• 406-96-2 2,2-Difluoroheptane 

Relevant articles and documents

Preparation method of methyl dihydrojasmonate

The invention discloses an efficient synthesis method of methyl dihydrojasmonate. Under catalysis of homogeneous rhodium and organic nitric oxide, 1-heptyne and ethylene have Pauson-Khand reaction, 2-amyl-2-cyclopentenone is rapidly and efficiently obtained, and an intermediate is subjected to addition and decarboxylation by dimethyl malonate to obtain the methyl dihydrojasmonate. The efficient synthesis method mainly has the advantages that 1-heptyne and ethylene Pauson-Khand reaction yield is effectively improved by the aid of the organic nitric oxide, and usage of rhodium catalysts is reduced. Compared with a traditional methyl dihydrojasmonate production method, the method has the advantages that route steps are short, atom economy is high, the cost is low, and the method is suitable for scale production of the methyl dihydrojasmonate.

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.